Thiophenol → Benzene, 1-methoxy-4-(phenylthio)-

HRID 2217030Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([S:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 7969Thiophenol

HCID 696764-Iodoanisole

Product 1

HCID 138547Benzene, 1-methoxy-4-(phenylthio)-

Procedure

The general procedure was used to convert 4-iodoanisole and thiophenol to the title product. Purification by flash chromatography (hexane/CH2Cl2 [3:1] as the eluent) gave the analytically pure product as a clear oil (416 mg, 96% yield). 1H NMR (300 MHz, CDCl3) δ 7.29 (dt, J=7.72, 2H; Ha, Ha′), 7.13–6.97 (m, 5H; Hc, Hc′, Hd, Hd′, He), 6.77 (d, J=7.54, 2H; Hb, Hb′), 3.67 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 159.74 (C4), 138.54 (C8), 135.29 (C2, C6), 128.85 (C9, C13), 128.08 (C10, C12), 125.66 (C11), 124.17 (C1), 114.90 (C3, C5), 55.23 (C7). Anal. Calcd. for C13H12OS: C, 72.19; H, 5.59; S, 14.82; Found C, 72.34; H, 5.70; S, 14.81.

Sources & evidence

ORD record: ord-ce3e2291830541f2b82665744414eef6
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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